


Do They Make You Feel Pretty?

by NaughtyPastryChef



Series: Orgasms For Everyone! spn Kinktober 2017 [9]
Category: Supernatural
Genre: Confident Sam, Dean in Panties, Dirty Talk, Exhibitionism, M/M, Masturbation, Panties
Language: English
Status: Completed
Published: 2017-10-10
Updated: 2017-10-10
Packaged: 2019-01-15 11:36:10
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,458
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12320277
Author URL: https://archiveofourown.org/users/NaughtyPastryChef/pseuds/NaughtyPastryChef
Summary: kintober day 9 prompt lingerie. Sam founds out about Dean's dirty little secret; they both like it.





	Do They Make You Feel Pretty?

“Hope I got the right kind, Samantha, I know how picky you get.” Dean laughed as he tossed a generic package emblazoned with “HANES” across the front of it in Sam’s face. He felt his cheeks flame at the shame of having his older brother buying his underwear but the shame quickly grew to outrage as he looked at the package.

“THESE ARE PANTIES YOU BUTTMUNCH!” He yelled, standing up with clenched fists. Dean was laughing so hard he was bent over at the waist and it took nothing to tackle him to the floor. They wrestled for a moment until Dean started to tickle him and then Sam fell apart, gasping for breath between his angry, pained laughter.

“Say uncle Sammy. C’mon, tell me who’s the winner. Say it!” Dean yelled into Sam’s face and he barely managed to get the words out through his tears. As they lay panting on the floor, both red faced, Sam thought about it again and punched Dean in the shoulder.

“You’re such a jerk, Dean. I needed boxers. What am I gonna do with those?”

“I got your boxers Sammy. Those were on super clearance and when I thought about the face I knew you’d make when I gave them to you I couldn’t resist. Use ‘em for whatever you want. Better than a sock for cleaning up after jerking off, right?” He punched Dean again, softer this time, and collapsed back into laughter.

And the package of panties was forgotten.

A few weeks later he was digging through Dean’s bag looking for a particular shirt that he was hoping that he hadn’t left behind in their last move, when his fingers touched something out of place. He grabbed the odd shape and in his hand was the shirt he’d been looking for and it was wrapped around something. He unfolded it slowly, very aware of the fact that Dean could come in at any minute and find him rifling through his stuff, when he gasped aloud. The package of the girls panties. It had clearly been opened and while two of the pairs were still clearly wrapped and untouched, two more had clearly been unwrapped and washed and one of the five was missing. He was so lost in his wondering about why Dean had kept them and why they were open that he didn’t hear his brother step into the room.

“What are you… huh. Well, found them, huh?” Sam whirled around, the shirt falling forgotten to the floor as he clutched at the package of panties in his hand. He stared at his big brother silently, wanting the answers to the questions running through his head but not really wanting to ask them.

“Gonna make fun of me, then? If you’re gonna do it, Sammy, do it and get it over with but don’t tell Dad, huh?” Dean looked defensive and scared.

“What?” Sam felt the word fall out of his mouth as he tried to puzzle out the explanation. What was Dean talking about? What was going on? What did Dean think he was going to make fun of him for? “What?” He repeated, as though he might get some more explanation.

“The panties. Look, sometimes I like to wear them, okay? It’s not that big of a deal. I mean, they’re soft and they feel real good on my junk, okay? I didn’t think you’d be a dick about it. I’m just asking you not to tell dad.”

Sam felt a flash of heat through his whole body and his dick start to chub up in his second-hand jeans. Dean liked to wear panties. Dean could, potentially, be wearing panties right now. His big, strong, masculine brother in pretty, frilly panties. Because they feel good on his junk. Because he likes them.

“Can I see?” That was most certainly not what he’d intended to come out of his mouth. He blinked and turned his head to look at himself in the mirror above Dean’s dresser. He looked as confused and as turned on as he felt, so that was somehow reassuring.

“You wanna see?” Sam was pretty sure that Dean’s voice had never been that high, even before he hit puberty and became the deep-voiced God that he currently was.

“I wanna see you in your panties.” Sam marveled at the flirt in his voice; at the confidence. He sounded a lot more confident than he felt. Dean was all he’d ever wanted in his life since he’d discovered what his dick was even for. Dean all gorgeous and pretty in some generic cotton panties was a fantasy come to life and it was a fantasy he’d never even dreamed up. Dean kicked his shoes off and tugged his shirt up over his head; Sam was momentarily distracted by the way it fluttered to the floor. He cut his eyes back to Dean who was back to looking insecure.

“Do they make you feel pretty?” Sam was not sure where the question came from but he couldn’t begin to regret it when Dean flushed all the way from his nipples, up his neck and onto the tops of his ears. Sam knew, without Dean having to tell him, that was his answer. 

Panties made Dean feel pretty and he liked it.

Sam licked his lips when Dean’s jeans fell to the floor around his feet with a soft sound and then he just sat there and looked his fill. There was nothing particularly sexy or racy about the panties, other than the fact that they were clearly ladies cotton panties on his very male brother. There was a little scalloping around the leg holes and at the waist and just a tiny bow at the top center, right above Dean’s cock. They arely contained everything that Dean had to offer and somehow that made it more appealing as well.

“Do you just like to wear them or do you  do other stuff in them?” Sam winced when his voice cracked; he’d meant to sound in control and confident and ended up sounding like a kid.

“Other stuff, like what Sammy?” Dean asked as he picked up each leg to step out of his jeans and stood there, totally bare except for the innocent white cotton.

“Other stuff like… touch yourself?” Even as he said it, he wasn’t sure if he was asking or telling.

Dean moved his right hand from where it hung next to his hip and cupped his cock through the panties. His lips parted on a gasp as he squeezed and massaged his dick to fullness within the cotton.

“Like this? Yeah, sometimes.” He didn’t stop and Sam didn’t want him to. He didn’t think he’d ever been as turned on as he was in that moment. Dean was so sexy all the time and this was just another layer of that on top of his usual sex appeal. He wanted Dean to get himself off in his panties. He wanted to go down on his knees in front of his brother and suck at the wet spot that he could see forming. He wanted to know what all that freckled skin tasted like. He licked his lips again and shifted his hips, feeling the drag of his own cock over the inside of his boxers; hot and tacky.

“Feels nice, you know? Panties are so soft on my skin. They cradle my ass and my balls just right. I like havin some dirty secret too. Walking around, looking all tough and ready to kill some monster and knowing that later on, Imma come back to wherever we’re crashing and pull off my jeans to see some pretty panties cradling my junk.” Dean was practically panting now and Sam was right there with him even without having laid a hand on himself.

“I like things that feel good, Sammy.” Dean added as his other hand moved to caress his balls in the cotton. Sam could see they were already drawn up tight, like Dean was about to cream the cotton already.

“Like your eyes on me. That always feels good Sammy. Love it when you watch me. Love the way you’re lookin at me right now. Fuck. Makes me just.” His voice cut out as he pinched the head of his dick and Sam could see the way that his shaft throbbed as the wetness spread through the thin fabric.

Sam was panting like he’d run a marathon. His throat was so dry that he had no words as Dean skimmed the soiled cotton down off his legs and held them, dangling, from one finger.

“Your turn Sammy. Question is; do you want a fresh pair, or do you wanna borrow mine?”


End file.
